Multifaceted palladium catalysts towards the tandem diboration-arylation reactions of alkenes.
Novel Pd(2) (6+) compounds have been synthesized in high yield. These compounds and their Pd(2) (4+) counterparts as synthetic precursors mediate the diboration of vinylarenes and aliphatic 1-alkenes, and under mild and basic reaction conditions they produce a variety of 1,2-diboronate esters with excellent conversions and chemoselectivities. The presence of bis(catecholato)diboron (B(2)cat(2)) favours the reduction of Pd(III) to Pd(II), while the catalytic precursor of Pd(II) is transformed into Pd(0)-nanoparticles. An "in situ" catalytic tandem reaction has been designed to transform the diboronate intermediates into the monoarylated product, which after oxidative workup, provides the carbohydroxylated adduct. Eventually, the same catalyst performs both sequences with total conversion from the alkene.
Penno
Dirk
D
Departament de Química Inorgànica, Universitat de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain.
Lillo
Vanesa
V
Koshevoy
Igor O
IO
Sanaú
Mercedes
M
Ubeda
M Angeles
MA
Lahuerta
Pascual
P
Fernández
Elena
E
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010316:Particle Size; D013237:Stereoisomerism; D013997:Time Factors
D000438:Alcohols; D000475:Alkenes; D001897:Boronic Acids; D009942:Organometallic Compounds; D010165:Palladium